Sodium Hydroxide → HCID 178512354, compound

HRID 1451066Notes

Reaction equation

HRID 1451066 reaction equation
[NH2:1][C:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11])=[N:3][C:4]#[N:5].[OH-].[Na+]>O>[OH2:11].[NH2:1][C:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11])=[N:3][C:4]#[N:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497936HCID 178497936, compound

Product 1

HCID 178512354HCID 178512354, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of methyl 3-[amino(cyanoiminomethyl)]aminobenzoate (7.3 g, 33.47 mmol) in 20 mL of deionized water was added 1N sodium hydroxide (34 mL, aqueous) and the mixture heated at reflux for 2 h. The resulting mixture was filtered and the filtrate neutralized with 6N HCl. The turbid solution was filtered and the clear filtrate further acidified using 6N HCl to pH 4.0-4.5. The white solid was separated through filtration, washed with 30 mL of water, dried in air followed by drying in a pistol at toluene reflux in vacuo to give 1.26 (18%) of the title compound, mp>300° C. Further acidification gave more solid 3.96 g (58%) which was slightly impure.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 h
  3. filtrationThe resulting mixture was filtered
  4. filtrationThe turbid solution was filtered
  5. customThe white solid was separated through filtration
  6. washwashed with 30 mL of water
  7. customdried in air
  8. dry with materialby drying in a pistol at toluene
  9. temperaturereflux in vacuo

Sources & evidence

ORD record
ord-8c0dc8e3e72b47f48c839556ae00cfbd
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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